TLC

Before Aaliyah and Monica helped shape what modern urban cool meant, TLC wrote the damn handbook. Chilli, T-Boz and Left-Eye took a few style cues from Salt-n-Pepa and En Vogue but made TLC's look at once both grittier and more visionary. In the classic "Waterfalls" clip, they sported typical 1990s streetwear (midriff-baring tops, roomy denim, tie-around jackets) as they literally walked on water. Personality was paramount; the ordinary could seem extraordinary in this group's hands.

In 1999's Hype Williams-directed "No Scrubs" video, the group underwent a huge image overhaul, now resembling post-ravers from a Japanimation thriller. Their futuristic looks reflected the themes of Fanmail, which itself reflected the technophilic concerns of the Y2K youth. Interestingly, TLC is now at the center of a nostalgic dialogue being excavated by a new generation: highly stimulated kids too young to properly remember when TRL was huge, but who wish they did. Armed with Tumblrs, lurid "future-vintage" mall-rat clothes, and a lot to prove, they are banking on personality carrying them a long way. Here's hoping they have the tunes to back it up.